Diethyl Ether → HCID 15398356, compound

HRID 1824636Notes

Reaction equation

HRID 1824636 reaction equation
[C-:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.[CH-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[Fe+2:19].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CCOCC>C(Cl)Cl>[C-:1]1([C:6]2[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=2)[CH:2]=[CH:3][CH:4]=[CH:5]1.[CH-:14]1[CH:18]=[CH:17][CH:16]=[CH:15]1.[Fe+2:19]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 131725737HCID 131725737, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 15398356HCID 15398356, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A sample of 4-ferrocenylbenzyl alcohol 16 (630 mg, 2.15 mmol) was added to a suspension of pyridinium chlorochromate (1.22 g, 3.23 mmol) in CH2Cl2 (5 mL) and the mixture was stirred under argon at rt for 18 h. Then Et2O (20 mL) was added and the mixture was filtered through a pad of Celite. The filtrate was concentrated and chromatographed (silica, CH2Cl2/hexanes, 4:1) affording 306 mg (47.8%). TLC (silica, CH2Cl2), Rf=0.35; mp 122–125° C. (lit.35a121–125° C.); 1H NMR δ 4.07 (s, 5H), 4.46 (A2B2, J=1.5 Hz, 2H), 4.47 (A2B2, J=1.5 Hz, 2H), 7.60,7.78 (AA′BB′, J=8.7 Hz, 4H), 9.97 (s, 1H); 13C NMR δ 67.8, 70.5, 70.6, 70.8, 127.0, 127.7, 130.7, 130.7, 134.7, 192.5; EI-MS obsd 290.0406 (M+), calcd exact mass 290.0394; Anal. Calcd for C17H14FeO: C, 70.37; H, 4.86; Found: C, 70.50; H, 4.81.

Workup

  1. filtrationthe mixture was filtered through a pad of Celite
  2. concentrationThe filtrate was concentrated
  3. customchromatographed (silica, CH2Cl2/hexanes, 4:1)
  4. customaffording 306 mg (47.8%)
  5. custommp 122–125° C. (lit.35a121–125° C.)

Sources & evidence

ORD record
ord-148819563a144424b5704bc7d86b4d6d
Source dataset
uspto-grants-2006_05
Patent number
US07042755B1

Reaction notes

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